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Answer by Tamara Wiens, in transition since 2012:
There are a number of different things to consider when thinking about why some trans women conform to societal stereotypes of femininity and whether that is a necessity for them to be considered women, either by themselves or by society. The short answer, cutting right to the chase, is: No, there is no need for any woman, cis or trans, to conform to any stereotype of femininity to still be a woman—the challenge truly comes from whether you are accepted as the woman that you claim to be.
Stereotypes are not always a bad thing—evolution actually shaped us to need and expect stereotypes as a way of staying safe. In a scary world, where we hairless apes had very few of the advantages of strength, agility, natural weapons, armor, and so on, we had to be able to quickly identify threats to our health and well-being and implement that other well-known human feature: the fight-or-flight response. In this situation, stereotypes are helpful: Does it growl loudly? Danger. Is it creepy and crawly? It will likely make our skin itch.
The problem comes when we mistake stereotypes for the things that they are intended to help us classify, or worse, when we believe in mistaken stereotypes and apply them to all members of that class that we believe are described by that mistaken stereotype. An example of the first problem is when we take a valid stereotype (women tend to be more maternal than men) and extend it to all members of the class “women” (Tamara is maternal). It may be true, or it may be completely wrong. An example of the second problem is the stereotype that women are bad drivers (most definitely not true, at least not based on drivers involved in serious accidents), and saying that Tamara is a bad driver because she is a woman.
When you see someone in Western societies in a “skirt” (any lower-body covering based on material wrapped around the waist and not divided for the legs), the stereotype tells us that we are looking at a woman. However, this is not always true: Scotsmen wear kilts (and calling it a skirt will cause you a high degree of pain when the Scotsman takes offense), and there are other cultures and regions where skirts are the norm for men (Middle Eastern/Arabic nations, Pacific island cultures). Another stereotype that has changed over the years is the wearing of hose; it used to be the province of men, in the late Middle Ages and Renaissance, that men wore tight-fitting lower garments over their legs. This hasn't been true in North America and Europe in a couple of hundred years and has switched to the other side, although women weren't allowed to display their stocking-clad legs in English-speaking nations until after the Victorian era. Today, if you see someone buying nylons, your immediate assumption is that they are for a woman.
When it comes to trans women, the challenges we face when dealing with gender stereotypes are numerous. We know what gender we are, and we have our internal sense of how we look and present to others. Many of us, particularly when we transition after puberty, are cursed with broad shoulders, large feet and hands, narrow hips, bearded faces, a prominent brow ridge, deeper voice, and so on. Late transitioners (like me, started transitioning at 45) also have challenges such as hair loss and decades of acculturation as a man, leading to patterns of behavior (speech, body language, how we walk, how we sit, etc) that are atypical for women in our societies.
For many of us, acceptance as women is just as important as our internal sense of gender; this acceptance is hard to come by when there are numerous cues, both conscious (behaviors, for example) and unconscious (shoulder width, height, brow ridge) that conspire against us. It is relatively easy to spot a man wearing women's clothing, dressed as a woman—unless he is an actor and has trained for the role, he's likely to pick inappropriate clothing, demonstrate discomfort with the clothes and role that he is playing, speak and act and walk and sit in ways that will out him as a “man in a dress and a wig” regardless of how flawless his presentation may be, from a two-dimensional perspective.
One way to overcome these cues is to modify all the conscious cues that we can (sit and walk demurely, speak appropriately, wear age-relevant and accepted clothing) and minimize all the unconscious cues to the degree that we are able (hairpieces for baldness, electrolysis for beards, clothing styles that flatter our height and hips, or de-emphasize our shoulders, holding our hands in ways that make them appear smaller)—in essence, aggressively conforming to every single stereotype for women that we can.
For a cis woman, who has the unconscious cues built in to her genetics, she can mess with the conscious cues and not be misgendered in most circumstances—in my experience, a butch woman is still a woman, no matter how unfeminine, stereotypically, her dress and behavior may be. For a trans woman, every cue that we miss on the conscious side just adds to the weight of the unconscious cues that we didn't fully mitigate. This leaves us in situations where we can't get access to the washrooms that we need, or where we can't find a romantic or sexual partner, or we get stared at and laughed at and generally marginalized, all because we didn't fit the stereotypes.
This isn't unique to trans women. Trans men, butch cis women, or flamboyant cis men face the same problems—for them, the challenge is that they can end up being identified as gay, even if they are quite definitely straight ... and not one bit of this should matter, either being trans, or gay, or just nonconforming in presentation. But it does. So, many trans women shape their eyebrows and wear makeup and skirts and have surgeries done to reshape their faces or to give them breasts—not because we necessarily buy into the stereotypes for our gender, but because the only way we will be accepted as women is if we conform to the stereotypes as much as possible.
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